1-Propanol → 4-(3,5-Bis(phenylethynyl)-phenyl)-2,3,5-triphenylcyclopentadienone

HRID 130653

반응식

HRID 130653 반응식
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([C:23]([C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=O)=O)[CH:12]=[C:13]([C:15]#[C:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:33]1([CH2:39][C:40]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(O)CC.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[C:13]([C:15]3[C:16]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[C:42]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[C:40](=[O:41])[C:39]=3[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:12]=[C:11]([C:23]#[C:25][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 10311-PropanolHCID 75931,3-Diphenyl-2-propanoneHCID 66854Benzyltrimethylammonium hydroxideHCID 223214133,5-Bis(phenylethynyl)benzil

생성물 1

HCID 223214114-(3,5-Bis(phenylethynyl)-phenyl)-2,3,5-triphenylcyclopentadienone수율 76.4%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
24 °C

실험 절차

A portion of the 3,5-bis(phenylethynyl)benzil (10.87 grams, 0.0265 mole), 1,3-diphenylacetone (5.90 grams, 0.0281 mole), anhydrous 1-propanol (300 milliliters) and anhydrous toluene (17 milliliters), both of which had been sparged with dry nitrogen, were added under a dry nitrogen atmosphere to a predried 500 milliliter glass three neck round bottom reactor containing a predried magnetic stirring bar. The reactor was additionally outfitted with a fan cooled spiral condenser and a thermometer with thermostatically controlled heating mantle. Stirring and heating commenced, and once a refluxing clear light yellow colored solution formed, benzyltrimethylammonium hydroxide (40 percent in methanol) (0.91 gram) was added, immediately inducing a dark red color. After maintaining the reflux for 20 reactant had been achieved. After a cumulative 30 minutes of reaction, the heating mantle was removed from the reactor, and the stirred contents were maintained at 24° C. for the next 16 hours. The product was recovered via filtration through a medium fitted glass funnel. The product cake on the funnel was washed with two portions (50 milliliters) of 1-propanol, then dried in a vacuum oven to provide 11.84 grams (76.4 percent isolated yield) of 4-(3,5-bis(phenylethynyl)phenyl)-2,3,5-triphenylcyclopentadienone (unsymmetrically substituted 3,5-AAB monomer) as a dark red purple colored crystalline product. HPLC analysis revealed the presence of the desired product at 100 area percent. The product's identity was confirmed by 1H NMR and El MS analysis.

후처리

  1. additioncontaining a predried magnetic stirring bar
  2. temperaturecooled spiral condenser
  3. temperaturea thermometer with thermostatically controlled heating mantle
  4. temperatureheating commenced
  5. customonce a refluxing clear light yellow colored solution formed
  6. temperatureAfter maintaining the
  7. temperaturereflux for 20 reactant
  8. customAfter a cumulative 30 minutes of reaction
  9. customthe heating mantle was removed from the reactor
  10. filtrationThe product was recovered via filtration through a medium
  11. customfitted glass funnel
  12. washThe product cake on the funnel was washed with two portions (50 milliliters) of 1-propanol
  13. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-f37d302ca74e47a0a6ce1e00354c92af
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381850B2

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